The specific aim of the research outlined in this proposal is to synthesize the antitumor antibiotic menogarol (A). The strategy is divided into three parts: (1) the preparation of benzoxocin B which comprises the DEF-rings of menogarol, (2) the annulation of the anthracycline rings onto B, and (3) the manipulation of the functionality in the A ring to give menogarol. The proposal also includes a section concerning the use of 4- and 5-silyl-substituted isoxazolidines for the synthesis of allylic amines and the pyrrolidine neurotoxins kainic acid (C) and allo-kainic acid (D). Silylisoxazolidines are prepared by the [3+2] dipolar cycloaddition of nitrones and vinylsilanes.